Acyl 1,3-migration in rhodium-catalyzed reactions of acetylenic β-ketoesters with aryl boronic acids: Application to two-carbon-atom ring expansions

Tomoya Miura; Masahiko Shimada; Masahiro Murakami

doi:10.1002/anie.200502650

Acyl 1,3-migration in rhodium-catalyzed reactions of acetylenic β-ketoesters with aryl boronic acids: Application to two-carbon-atom ring expansions

Tomoya Miura, Masahiko Shimada, Masahiro Murakami

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

(Chemical Equation Presented) Expanding rings: An intermediate organorhodium(I) species formed in the Rh^I-catalyzed reaction of acetylenic β-ketoesters and β-diketones with aryl boronic acids undergoes intramolecular nucleophilic addition to a ketone carbonyl group. The ensuing ring-opening reaction of the resulting cyclobutanols results in acyl 1,3-migration leading to the development of a two-carbon-atom ring-expansion reaction.

Original language	English
Pages (from-to)	7598-7600
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	46
DOIs	https://doi.org/10.1002/anie.200502650
Publication status	Published - Nov 25 2005
Externally published	Yes

Keywords

Acyl migration
Boron
Cyclizations
Rhodium
Ring expansion

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200502650

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abstract = "(Chemical Equation Presented) Expanding rings: An intermediate organorhodium(I) species formed in the RhI-catalyzed reaction of acetylenic β-ketoesters and β-diketones with aryl boronic acids undergoes intramolecular nucleophilic addition to a ketone carbonyl group. The ensuing ring-opening reaction of the resulting cyclobutanols results in acyl 1,3-migration leading to the development of a two-carbon-atom ring-expansion reaction.",

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author = "Tomoya Miura and Masahiko Shimada and Masahiro Murakami",

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doi = "10.1002/anie.200502650",

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T1 - Acyl 1,3-migration in rhodium-catalyzed reactions of acetylenic β-ketoesters with aryl boronic acids

T2 - Application to two-carbon-atom ring expansions

AU - Miura, Tomoya

AU - Shimada, Masahiko

AU - Murakami, Masahiro

PY - 2005/11/25

Y1 - 2005/11/25

N2 - (Chemical Equation Presented) Expanding rings: An intermediate organorhodium(I) species formed in the RhI-catalyzed reaction of acetylenic β-ketoesters and β-diketones with aryl boronic acids undergoes intramolecular nucleophilic addition to a ketone carbonyl group. The ensuing ring-opening reaction of the resulting cyclobutanols results in acyl 1,3-migration leading to the development of a two-carbon-atom ring-expansion reaction.

AB - (Chemical Equation Presented) Expanding rings: An intermediate organorhodium(I) species formed in the RhI-catalyzed reaction of acetylenic β-ketoesters and β-diketones with aryl boronic acids undergoes intramolecular nucleophilic addition to a ketone carbonyl group. The ensuing ring-opening reaction of the resulting cyclobutanols results in acyl 1,3-migration leading to the development of a two-carbon-atom ring-expansion reaction.

KW - Acyl migration

KW - Boron

KW - Cyclizations

KW - Rhodium

KW - Ring expansion

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Acyl 1,3-migration in rhodium-catalyzed reactions of acetylenic β-ketoesters with aryl boronic acids: Application to two-carbon-atom ring expansions

Abstract

Keywords

ASJC Scopus subject areas

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